Diastereoselective Carbonyl Allylation with Simple Olefins Enabled by Palladium Complex-Catalyzed C–H Oxidative Borylation

A highly
diastereo­selective Pd-catalyzed carbonyl allyl­ation
of aldehydes and isatins directly using simple acyclic olefins as
allyl­ating reagents is described. This transformation is actually
a sequential process consisting of a Pd-catalyzed oxidative allylic
C–H borylation and an allyl­boration of carbonyls accelerated
by phosphoric acid, wherein a wide scope of olefins could be tolerated.
The oxidant is revealed to play a key role in the successful realization
of the allylic C–H activation-based allylation.